Nirmatrelvir: Difference between revisions

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[[File:PF-07321332.svg|Chemical structure of Nirmatrelvir|thumb]]
{{Infobox drug
[[File:Xray_crystal_structure_PDB-7si9.png|X-ray crystal structure of Nirmatrelvir|thumb]]
| drug_name          = Nirmatrelvir
| INN                = Nirmatrelvir
| type              = Antiviral medication
| image              = PF-07321332.svg
| width              = 250
| alt                = Skeletal formula of Nirmatrelvir
| caption            = Skeletal structure of Nirmatrelvir
 
<!-- Clinical data -->
| pronounce          = {{IPAc-en|n|ɜːr|ˈ|m|æ|t|r|əl|v|ɪər}}<br />{{respell|nur|MAT|rəl|veer}} or {{IPAc-en|ˌ|n|ɜːr|m|ə|ˈ|t|r|ɛ|l|v|ɪər}}<br />{{respell|NUR|mə|TREL|veer}}
| tradename          = Paxlovid (in combination with ritonavir)
| Drugs.com          = [https://www.drugs.com/monograph/nirmatrelvir.html Monograph]
| MedlinePlus        = a622026
| licence_EU        = Yes
| DailyMedID        = Nirmatrelvir
| licence_US        = Yes
| pregnancy_AU      = B3
| pregnancy_AU_comment =
| pregnancy_category = Not assigned (US)
| routes_of_administration = [[Oral administration|By mouth]]
| class              = Protease inhibitor; Antiviral
| ATCvet            =
| ATC_prefix        = J05
| ATC_suffix        = AE10
| ATC_supplemental  =
 
<!-- Legal status -->
| legal_AU          = S4
| legal_AU_comment  =
| legal_BR          = C1
| legal_BR_comment  =
| legal_CA          = Rx-only
| legal_CA_comment  =
| legal_DE          = Rx-only
| legal_DE_comment  =
| legal_NZ          = Prescription only
| legal_NZ_comment  =
| legal_UK          = POM
| legal_UK_comment  =
| legal_US          = Rx-only
| legal_US_comment  =
| legal_EU          = Rx-only
| legal_EU_comment  =
| legal_UN          =
| legal_UN_comment  =
| legal_status      = Prescription only in most countries
 
<!-- Pharmacokinetic data -->
| bioavailability    = Unknown
| protein_bound      = ~69%
| metabolism        = Hepatic (CYP3A inhibition affects clearance)
| metabolites        = Minimal metabolism
| onset              = Within hours
| elimination_half-life = ~6 hours (with ritonavir)
| duration_of_action = 12 hours
| excretion          = Feces and urine
 
<!-- Identifiers -->
| CAS_number        = 2628280-40-8
| CAS_supplemental  =
| PubChem            = 155903259
| IUPHAR_ligand      =
| DrugBank          = DB16691
| ChemSpiderID      = 114826566
| UNII              = 7R9A5P7H32
| KEGG              = D12244
| ChEBI              = 170007
| ChEMBL            =
| NIAID_ChemDB      =
| PDB_ligand        =
| synonyms          = PF-07321332
 
<!-- Chemical and physical data -->
| IUPAC_name        = (1R,2S,5S)-N-[(1S)-1-cyano-2-[(3S)-2-oxopyrrolidin-3-yl]ethyl]-3-[(2S)-3,3-dimethyl-2-[(2,2,2-trifluoroacetyl)amino]butanoyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide
| C                  = 23
| H                  = 32
| F                  = 3
| N                  = 5
| O                  = 4
| SMILES            = CC1([C@@H]2[C@H]1[C@H](N(C2)C(=O)[C@H](C(C)(C)C)NC(=O)C(F)(F)F)C(=O)N[C@@H](C[C@@H]3CCNC3=O)C#N)C
| StdInChI          = 1S/C23H32F3N5O4/c1-21(2,3)16(30-20(35)23(24,25)26)19(34)31-10-13-14(22(13,4)5)15(31)18(33)29-12(9-27)8-11-6-7-28-17(11)32/h11-16H,6-8,10H2,1-5H3,(H,28,32)(H,29,33)(H,30,35)/t11-,12-,13-,14-,15-,16+/m0/s1
| StdInChI_comment  =
| StdInChIKey        = LIENCHBZNNMNKG-OJFNHCPVSA-N
| density            = Unknown
| density_notes      =
| melting_point      = 192.9 °C
| melting_high      =
| melting_notes      =
| boiling_point      = Not applicable (decomposes)
| boiling_notes      =
| solubility        = Slightly soluble in water
| sol_units          =
| specific_rotation  =
}}
[[File:PF-07321332.svg|Chemical structure of Nirmatrelvir|thumb|left]]
[[File:Xray_crystal_structure_PDB-7si9.png|X-ray crystal structure of Nirmatrelvir|left|thumb]]
[[File:PF-07321332_synthesis.svg|Synthesis pathway of Nirmatrelvir|thumb]]
[[File:PF-07321332_synthesis.svg|Synthesis pathway of Nirmatrelvir|thumb]]
'''Nirmatrelvir''' is an [[antiviral drug]] currently under development by [[Pfizer]] for the treatment of [[COVID-19]]. It is a part of a combination therapy with [[Ritonavir]], another antiviral drug, and is being marketed under the brand name '''Paxlovid'''.  
'''Nirmatrelvir''' is an [[antiviral drug]] currently under development by [[Pfizer]] for the treatment of [[COVID-19]]. It is a part of a combination therapy with [[Ritonavir]], another antiviral drug, and is being marketed under the brand name '''Paxlovid'''.  

Revision as of 00:18, 25 March 2025

Nirmatrelvir
Skeletal formula of Nirmatrelvir
INN Nirmatrelvir
Drug class Protease inhibitor; Antiviral
Routes of administration By mouth
Pregnancy category Not assigned (US)
Bioavailability Unknown
Metabolism Hepatic (CYP3A inhibition affects clearance)
Elimination half-life ~6 hours (with ritonavir)
Excretion Feces and urine
Legal status Prescription only in most countries
CAS Number 2628280-40-8
PubChem 155903259
DrugBank DB16691
ChemSpider 114826566
KEGG D12244
File:PF-07321332.svg
Chemical structure of Nirmatrelvir
File:Xray crystal structure PDB-7si9.png
X-ray crystal structure of Nirmatrelvir
File:PF-07321332 synthesis.svg
Synthesis pathway of Nirmatrelvir

Nirmatrelvir is an antiviral drug currently under development by Pfizer for the treatment of COVID-19. It is a part of a combination therapy with Ritonavir, another antiviral drug, and is being marketed under the brand name Paxlovid.

Mechanism of Action

Nirmatrelvir works by inhibiting the main protease (Mpro) of the SARS-CoV-2 virus. Mpro is an essential enzyme for the virus, playing a crucial role in mediating viral replication and transcription processes. By inhibiting this enzyme, Nirmatrelvir prevents the virus from multiplying within the host's body.

Development and Approval

The development of Nirmatrelvir began in early 2020, shortly after the onset of the COVID-19 pandemic. Pfizer utilized a structure-based drug design approach to develop this novel antiviral. In November 2021, Pfizer applied for Emergency Use Authorization (EUA) from the U.S. Food and Drug Administration (FDA) for Nirmatrelvir in combination with Ritonavir for the treatment of mild-to-moderate COVID-19 in individuals at high risk of progressing to severe disease.

Clinical Trials

Several clinical trials have been conducted to evaluate the safety and efficacy of Nirmatrelvir. The most notable of these is the EPIC-HR trial, a Phase 2/3 randomized, double-blind, placebo-controlled trial. The trial demonstrated a significant reduction in the risk of hospitalization or death in patients treated with Nirmatrelvir and Ritonavir compared to placebo.

Side Effects

Common side effects of Nirmatrelvir include nausea, diarrhea, and vomiting. Serious side effects are rare but can include hepatotoxicity and severe allergic reactions.

See Also


RNA virus antivirals (primarily J05, also S01AD and D06BB)
Hepatitis C
NS3/4A protease inhibitors (–previr)
NS5A inhibitors (–asvir)
NS5B RNA polymerase inhibitors (–buvir)
Combination drugs
Hepatitis D
Picornavirus
Anti-influenza agents
Multiple/general


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